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How Square Transformed Sales Enablement with a Killer Content Strategy

After all, how effective can a training program be without the right sales content in place? From mobilizing “Subject Matter Experts” for content creation to identifying the right content pieces at each on-boarding stage, Charles Derupe (Sales Tools & Content Manager, Square) discusses 3 must-do’s when designing content for your sales enablement programs: Alignment, Access and Application.

Here are the 4 top takeaways from the webinar:

1. When designing your content strategy, start by mapping out your customer journey

Charles: When building out your go-to-market strategy, you have to think about how and when your buyers are buying your product, what the journey looks like and how they interact with the overall market.

At Square, we’re always mapping and re-mapping out the customer journey, because it’s constantly changing with every product launch. To keep up with this change, we really strive to understand the priorities with our content strategy by identifying the “perception” in the market. We do this by conducting qualitative surveys and interviews with our sales reps, since they’re at the front line of every deal. We collect data on where some of the roadblocks are and what tools they might need to succeed– then take these data points and map them to the customer journey to figure out where the pain points are happening. This paints a clear picture of where your enablement team needs to focus to make sure reps are successful throughout the cycle.

2. Your content strategy should involve marketing, core sales leadership and on-the-floor champions

Charles: Especially at a hyper growth company, cross-functional alignment is critical to create a consistent message and break the silos. Marketing needs to align on inbound messaging and content creation, your core sales leadership should help you implement all your hard work and advocates/champions on the floor will help you with adoption.

For the ‘order of operations’, I always start with the core sales leadership. It’s important to get their buy-in to understand the strategy and kickstart conversations with Marketing at the executive level. You should work with Marketing to identify shared goals, align on inbound positioning and set the foundation for consistent messaging across the board. After you’ve created the content, take it back to sales leadership and get their buy-in to help with implementation. Then, socialize it to the reps, make sure everything’s implemented correctly and get feedback from your on-the-floor champions.

3. Consistency is key for cross-functional alignment

Charles: It’s critical to agree on a core set of deliverables for Marketing to produce at every product launch. When a new PMM joins the company, I setup a meeting with the PMM and the PM, introduce myself as the one of the primary contact for GTM launches and agree on a core list of deliverables for every launch that include: a specific set of articles for Guru (our internal knowledge system), one-pager collateral, pitch deck to help us understand values and an internal training session. Case study is usually a nice-to-have.

Our leadership team appreciates this because it shows that we have a consistent go-to-market strategy and messaging for content. And the reps love this because they know that at every product launch, they’ll have a core set of materials to help them get ready. Consistency is key.

4. Key metrics to measure ROI: viewership, adoption and engagement

Charles: At the end of the day, you want to create a robust content ecosystem. Your reps should know how to use the content, why they need to use them and who they need to distribute them to.

Viewership/Adoption: Figure out if reps are looking at your content, who’s looking at what pieces and identify your ‘content champions’ to help socialize and gather feedback. Bonus points for tracking who’s not using the content and/or not applying it!

Engagement: Are reps talking about this piece of content? Are folks posting this / using this in their templates, and are content-rich templates performing better than bare-bone templates? Are your reps looking for more similar content?


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